Hydrochloric Acid → HCID 22805892, compound

Participants

Reaction Steps

24.05 g (0.121 mol) of o-acetoxybenzoyl chloride in 50 ml of anhydrous ether, and 17 ml (0.121 mol) of pure triethylamine in 18 ml of iced water, were added simultaneously over the course of 0.5 hr, at -2° C. ± 1° C., whilst stirring so as to produce emulsification, to a solution of 15.9 g (0.121 mol) of 4-hydroxy-L-proline in 42 ml of water and 17 ml (0.121 mol) of pure triethylamine. Stirring was continued for 0.75 hr at the same temperature and then for 25 minutes at ambient temperature. The pH was reduced from 7 to 3 by adding 9.8 ml of 12.35 N HCl (0.121 mol). The milky cloudiness was extracted with a total of 900 ml of pure ethyl acetate and the combined organic extracts were dried over anhydrous Na2SO4 and then concentrated in vacuo to give, in 2 to 3 successive crops, 23 g of the desired product (65% yield).

Provenance & Evidence